Water → 2,2'-((Phenylmethyl)imino)bisethanol

HRID 1006437Notes

Reaction equation

HRID 1006437 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[OH:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][OH:7])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8113DiethanolamineHCID 11430Potassium Carbonate

Product 1

HCID 75532,2'-((Phenylmethyl)imino)bisethanolYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bis(2-hydroxyethyl)amine (5 g) was dissolved in N,N-dimethylformamide (100 ml), added with benzyl bromide (6.52 ml) and potassium carbonate (8.657 g) and stirred at room temperature for 21 hours. The reaction mixture was added with water (200 ml) and extracted twice with dichloromethane (200 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: dichloromethane:methanol=20:1→10:1) to obtain 7.631 g of the title compound. Yield: 75%.

Workup

  1. extractionextracted twice with dichloromethane (200 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: dichloromethane:methanol=20:1→10:1)

Sources & evidence

ORD record
ord-569344e0d51f4e48b68ee658b982491e
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

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